Methyl iodide → HCID 67281758, compound

HRID 913037Notes

Reaction equation

HRID 913037 reaction equation
CI.[CH2:3]([O:10][C:11]1[C:16](=[O:17])[C:15]([CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:14][NH:13][C:12]=1[CH3:23])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:24](=O)([O-])[O-].[K+].[K+]>C(#N)C.ClCCl>[CH2:3]([O:10][C:11]1[C:16](=[O:17])[C:15]([CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:14][N:13]([CH3:24])[C:12]=1[CH3:23])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67282712HCID 67282712, compound

Product 1

HCID 67281758HCID 67281758, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl iodide (11 mL, 176 mmol) was added to a suspension of 3-benzyloxy-2-methyl-5-(2,2,2-trifluoro-ethyl)-1H-pyridin-4-one (1.18 g, 4.0 mmol) and potassium carbonate (1.06 g, 7.7 mmol) in acetonitrile (25 mL). The resulting mixture was heated to reflux, and the reaction was completed within 40 min. The mixture was cooled to RT, and the solid particulates was filtered off. The filtrate was concentrated in vacuo to give a solid. The solid was taken up in dichloromethane, and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 3-benzyloxy-1,2-dimethyl-5-(2,2,2-trifluoro-ethyl)-1H-pyridin-4-one as a colorless oil (1.3 g, 95% yield, HPLC Method 1 (Example 24), RT=15.9 min, HPLC purity (peak percent area): 98% at λ=280 nm).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. filtrationthe solid particulates was filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a solid
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3531663430e6481b84c1b2bf55e42866
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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